Synthesis of N-Benzyl-2-azanorbornene via Aqueous Hetero Diels-Alder Reaction

Author Contact: l.delaude@ulg.ac.be

Summary

This lab demonstrates a pericyclic reaction that is popular in undergraduate texts, the Diels-Alder reaction, and does so in the context of using water as a safe, alternative solvent. Adapted from work published by Larsen and Grieco in 1985, this experiment makes use of the synthesis of N-benzyl-2-azanorbornene to present green chemistry to students. Not only is this very atom economical reaction performed in water, but the starting materials are fairly low in toxicity, the yields are good and the product does not persist in the environment.

Easily accomplished in a four-hour lab period, this straightforward experiment introduces students to aqueous chemistry, liquid-liquid extractions, drying agents, rotary evaporation, and IR and proton and carbon-13 NMR spectroscopies.

Supplemental information includes an introduction to the Diels-Alder reaction and green chemistry, lab questions, an experimental procedure, spectroscopic data and structural analysis. Also, a poster and slide shows are available in a variety of formats.

Summary prepared January 2009 by Douglas M. Young at the University of Oregon.

Category Descriptors

Chemistry Concepts

• Alkenes
• Amines-Ammonium Compounds
• Aqueous Solution Chemistry
• Heterocycles
• Molecular Modeling
• Pericyclic Reactions
• Stereochemistry

Laboratory Techniques

• Extraction
• Extraction and Drying Agents
• Heating and Cooling Methods
• IR Spectroscopy
• Measuring Mass and Volume
• NMR Spectroscopy
• pH
• Rotary Evaporation

Green Chemistry Principles

• Design for Degradation
• Maximize Atom Economy
• Minimize the Potential for Accidents
• Prevent Waste
• Use Safer Solvents/Reaction Conditions

Chemistry Subdiscipline

• Organic Chemistry

Target Audience

• Colleges/Universities

Source

• Journal Articles